Dimethylcarbamoyl chloride, chemical formula C3H6ClNO, CAS 79-44-7. At room temperature, it is a colorless to slightly yellow liquid state and is a non volatile liquid. The common form is colorless transparent liquid. Its appearance can be similar to that of common Organochlorine chemistry. Due to the strong irritancy of DMF-Cl, its odor is usually described as pungent or pungent. It is almost insoluble in water and reacts with water to form dimethylaminoformic acid. However, it has good solubility in many organic solvents, such as ether, chloroform, methanol, ethanol, etc. This solubility makes DMF-Cl widely applicable in organic synthesis and chemical reactions. It does not easily evaporate at room temperature and can be stored and processed in liquid form. It should be noted that due to its irritating odor and corrosive properties, appropriate safety measures need to be taken during use and handling. It can be used as a synthetic intermediate for dyes and pigments, and can obtain amino formamide dyes with different colors, widely used in fields such as textiles, leather, ink, and plastics. It is also commonly used in chemical analysis to enhance the detection sensitivity of target compounds in chromatographic analysis.
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Chemical Formula |
C3H6ClN |
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Exact Mass |
10 |
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Molecular Weight |
10 |
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m/z |
107 (100.0%), 109 (32.0%), 108 (3.2%), 110 (1.0%) |
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Elemental Analysis |
C, 33.51; H, 5.62; Cl, 32.97; N, 13.03; O, 14.88 |
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The laboratory synthesis method of Dimethylcarbamoyl chloride (also known as DMF-Cl) typically uses Dimethylformamide (DMF) and Thionyl chloride (SOCl2) or Phosgene (COCl2). The preparation method of dimethylaminoformyl chloride comprises the following steps: dimethylamine and photocatalyst are introduced into a micro reactor for reaction to obtain dimethylaminoformyl gas The content of dimethylaminoformyl chloride prepared by the preparation method is as high as 98.5% ~ 99%, and the yield is greatly improved, reaching 95.0% ~ 96.2% (dimethylamine meter) The preparation method of the invention has the advantages of simple operation, high yield, less three wastes, safety and environmental protection, and is suitable for industrial production and has good application value and application prospect.
Step:
The chemical reaction formula for the reaction between Dimethylformamide and Thionyl chloride is as follows:
(CH3)2NC(O)H+SOCl2 → (CH3)2NCOCl+SO2+HCl
Prepare an anhydrous environment in a dry inert atmosphere, such as nitrogen or a dry solvent. Ensure that all instruments, containers, and reagents are dry.
Mix Dimethylformamide (DMF) and Thionyl chloride (SOCl2) in molar ratio. Usually, 1 equal mole of DMF is used to correspond to 2 equal moles of SOCl2.
Slowly add the prepared mixture to the cooled anhydrous solvent (such as dichloromethane or benzene). Stir the reaction mixture and control the reaction temperature, usually under conditions below room temperature. As the reaction progresses, you will observe gas release (SO2) and the reaction solution becoming turbid.
The reaction time varies depending on the experimental conditions, usually several hours. When the turbid reaction mixture gradually clears, it indicates that the reaction is nearing completion.
After the reaction is completed, the target product it is separated by distillation or filtration. Usually, it is necessary to remove the solvent and purify the product.
Melting point − 33 ° C (lit.), Boiling point 167-168 ° c775 mm Hg (lit.), Density 1.168 g / ml at 25 ° C (lit.), Refractive index N20 / D 1.453, Flash point 155 ° f, Acidity coefficient (PKA) - 1.85 ± 0.70 (predicted), Form liquid, Specific gravity 1.172, Water soluble decomposes, Sensitivity.
Dimethylcarbamoyl chloride (also known as DMF-Cl) is an organic compound with multiple uses.
DMF-Cl is an important intermediate in organic synthesis. It can be used as an aminoacylation reagent to introduce dimethylaminoformyl (DMF-CO) into other compounds. By reacting it with Aromatic amine or alcohol, corresponding N, N-dimethylcarbamide derivatives can be synthesized. In addition, it can also participate in reactions such as esterification, etherification, acylation, etc., and be used to construct complex organic molecules.
In organic synthesis and transformation, as an electrophilic reagent, the compound can participate in many Electrophilic substitution, Acylation, etc. For example, when it Substitution reaction with Aromatic amine, N, N-dimethylaminoamide can be obtained, which is widely used in pharmaceutical chemistry. The chlorine atom in the compound can be transformed into an iodine compound under the action of Sodium iodide, or into the corresponding carboxylic acid unit under alkaline conditions. In addition, acyl chloride can react with Hydroxylammonium chloride to obtain corresponding amide compounds.
Due to its chemical activity, DMF-Cl has a wide range of applications in the field of pharmaceutical manufacturing. For example, it can be used to synthesize protective groups in polypeptide drugs, such as arginine dimethyl carbamoyl ester (Dde) Protecting group. In addition, DMF-Cl can also be used to synthesize 5-aza-2 '- Deoxyuridine and other compounds, which have anti-tumor, antiviral and other activities.
DMF-Cl is widely used in the manufacturing of pesticides. For example, it can be used as a synthetic fungicide, such as DMFU, to protect crops from fungi and bacteria. In addition, it can also be used to synthesize other types of pesticide intermediates, such as insecticides and herbicides.
Dimethylcarbamoyl chloride is also commonly used in chemical analysis. It can be used for derivatization reactions to enhance the detection sensitivity of target compounds in chromatographic analysis. For example, by reacting with amines or alcohols, they are converted into corresponding N, N-dimethylaminoformamide derivatives, making them easier to detect in gas or liquid chromatography analysis.
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Uracile triphosphate UTP dimethylaminoformyl chloride itself is not directly used as an insecticide, but rather as a pesticide chemical intermediate, playing a key role in the synthesis of carbamate insecticides. Therefore, it is not accurate to directly discuss the insecticidal principle of dimethylaminoformyl chloride as an insecticide, but we can explore the insecticidal principle of amino ester insecticides synthesized as intermediates.
Insecticidal principle
Aminomethyl ester insecticides are an important class of organic synthetic pesticides, and their insecticidal mechanism is mainly based on the following aspects:
1. Inhibit cholinesterase activity
The main mechanism of action of carbamate insecticides is to exert insecticidal effects by inhibiting the activity of cholinesterase (ChE) in insects. Acetylcholinesterase is an important enzyme in insects, responsible for hydrolyzing the neurotransmitter acetylcholine (ACh) to maintain the normal transmission of nerve impulses. When carbamate insecticides enter the insect body, they bind with acetylcholinesterase to form carbamoyl acetylcholinesterase. This complex cannot hydrolyze acetylcholine anymore, leading to the accumulation of acetylcholine on the postsynaptic membrane.
The accumulation of acetylcholine can cause disturbances in insect nerve conduction, manifested as prolonged or blocked transmission of nerve impulses. This disorder in nerve conduction can lead to a series of toxic symptoms in insects, such as excitement, spasms, paralysis, etc., ultimately resulting in insect death. Due to the reversible inhibitory effect of carbamate insecticides on cholinesterase, meaning that the cholinesterase in insects can recover its activity after a period of time, the toxicity of these insecticides is relatively low and their pollution to the environment is also minimal.
2. Affects the process of nerve conduction
In addition to directly inhibiting cholinesterase activity, carbamate insecticides may also affect insect nerve conduction processes through other pathways. For example, they may interfere with the synthesis, release, or reuptake of neurotransmitters, thereby altering the excitability and conductivity of neurons. These changes will further affect the physiological activities and behavioral manifestations of insects, such as feeding, movement, reproduction, etc., ultimately leading to insect death or a decrease in population size.
Application characteristics of carbamate insecticides
1. Efficiency
Aminomethyl ester insecticides have efficient killing effects on various pests, including aphids, leafhoppers, planthoppers, cotton bollworms, tobacco aphids, beet armyworms, etc. These pests pose a serious threat to crops, and the use of carbamate insecticides can effectively control their numbers, protecting the growth and yield of crops.
2. Low toxicity
Compared with traditional insecticides such as organophosphates, carbamate insecticides have lower toxicity. They are less toxic to mammals and birds, and have less pollution to the environment. Therefore, it is relatively safe to use and has minimal impact on the ecological environment.
3. Strong selectivity
Aminomethyl ester insecticides have strong selectivity towards pests and minimal impact on natural enemies and beneficial organisms. This allows them to be combined with other biological control methods in agricultural production, forming a comprehensive control system that improves control effectiveness and reduces environmental damage.
Dimethylcarbamoyl chloride (DMCC) is an important organic synthetic intermediate widely used in the fields of pesticides, pharmaceuticals, and polymer chemistry. Its chemical structure consists of a dimethylaminoformyl group ((CH3) ₂ N-CO -) and a highly reactive chlorine atom, making it an ideal reagent for acylation reactions. The discovery of DMCC can be traced back to organic chemistry research in the late 19th century, but industrial production was not achieved until the mid-20th century. Due to its high reactivity and potential carcinogenicity, the application of DMCC is strictly regulated.
- In 1873, French chemist Charles Adolphe Wurtz first reported the synthesis of carbamoyl chloride (H ₂ N-CO-Cl), but the compound was extremely unstable.
- In the 1890s, the German chemist Emil Fischer's team attempted to synthesize DMCC for the first time by reacting dimethylamine ((CH3) ₂ NH) with phosgene (COCl ₂), but with low yield.
- In 1912, British chemist William Perkin Jr. optimized the synthesis method of DMCC by reacting dimethylformamide (DMF) with phosgene, increasing the yield to 60%.
- In the 1930s, with the development of organic chemistry theory, DMCC was confirmed as an effective reagent for Friedel Crafts acylation reactions.
- In 1945, the German company IG Farben (later split into BASF) developed the continuous phosgene method, significantly increasing the production of DMCC
- (CH3)2NH+COCl2→(CH3)2N−CO−Cl+HCl
- In the 1950s, DuPont introduced this process into pesticide production for the synthesis of carbamate insecticides.
Frequently Asked Questions
What is Dimethylcarbamoyl chloride used for?
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Dimethylcarbamoyl chloride is used as an intermediate in the production of pharmaceuticals, pesticides, and dyes. Acute (short-term) inhalation exposure to dimethylcarbamoyl chloride has been observed to result in damaged mucous membranes of the nose, throat, and lungs, and cause difficulty in breathing in rats.
Is dimethylamine hydrochloride toxic?
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It can stimulate the nervous system and cause irritation to the eyes, nose, and throat. Symptoms of high exposure include headache, dizziness, nausea, vomiting, diarrhea, shortness of breath, and coughing. Dimethylamine hydrochloride may also lead to skin irritation and allergic reactions.
Is dimethylamine carcinogenic?
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Effects of long-term or repeated exposure
Repeated or prolonged contact may cause skin sensitization. TLV: 5 ppm as TWA; 15 ppm as STEL; (DSEN); A4 (not classifiable as a human carcinogen).
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